Gartner Expert

Shayne Jackson

VP Analyst

Shayne Jackson is focused on the evolution of Enablement, Sales Talent Management, and Sales Culture. He serves as a strategic advisor to sales executives and enablement leaders on modernizing learning, content, and tools through a programmatic approach that drives sustained seller behavior change.

His primary research focus is driving rapid, high-impact organizational changes that align with commercial performance goals. Shayne's holistic approach leverages his extensive global leadership experience to help clients navigate:

• Sales Enablement Strategy: Designing impactful functions that shift from tactical support to technology-centered orchestrators of the sales motion.

• Enablement Effectiveness: Implementing modern behavior change strategies and measurement frameworks to demonstrate commercial impact.

• Sales Transformation and Culture: Aligning seller and manager mindsets with core values through strategic planning, messaging, and engagement.

• Talent Development: Designing onboarding programs that accelerate time-to-productivity and continuous learning models that leverage advanced technology for skill mastery.

Previous experience

Shayne has over 25 years of global experience in a wide range of sales roles. Before joining Gartner, he established and led sales enablement functions, managed channel partners and supported sales teams at EMC (now Dell Technologies), SimpliVity (acquired by HPE) and Applause.

Professional background

Applause, Senior Director of Sales Enablement, 2 years

SimpliVity (acquired by HPE), Director of Sales Enablement, 2 years

EMC Corporation (acquired by Dell Technologies), Director of Sales Enablement, Global Financial Services, 20 years

Areas of coverage
  • CSO Effectiveness

  • Operations and Decision Making

  • Talent Management

Education

M.B.A., Information Technology and Management, Clark University, Worcester, Massachusetts

B.A., Psychology, Boston College, Boston, Massachusetts

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Top Issues That I Help Clients Address

01

Establishing an impactful sales enablement function that drives change in the sales organization

02

Designing and deploying effective sales training

03

Identifying opportunties for and delivering sales culture transformation

04

Designing new hire training that accelerates sellers' ramp to productivity

05

Measuring the impact of sales enablement programs